WO2004111164A1 - Method for the production of fatty acids having a low trans-fatty acid content - Google Patents

Method for the production of fatty acids having a low trans-fatty acid content Download PDF

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Publication number
WO2004111164A1
WO2004111164A1 PCT/US2004/018586 US2004018586W WO2004111164A1 WO 2004111164 A1 WO2004111164 A1 WO 2004111164A1 US 2004018586 W US2004018586 W US 2004018586W WO 2004111164 A1 WO2004111164 A1 WO 2004111164A1
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WIPO (PCT)
Prior art keywords
fatty acid
oil
isomer
frans
hydrolysis
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PCT/US2004/018586
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English (en)
French (fr)
Inventor
Paul D. Bloom
Inmok Lee
Peter Reimers
Original Assignee
Archer-Daniels-Midland Company
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Filing date
Publication date
Application filed by Archer-Daniels-Midland Company filed Critical Archer-Daniels-Midland Company
Priority to JP2006533720A priority Critical patent/JP4571144B2/ja
Priority to BRPI0410668-7A priority patent/BRPI0410668B1/pt
Priority to KR1020057022439A priority patent/KR101050437B1/ko
Priority to EP04754992A priority patent/EP1631649B1/en
Priority to MXPA05012254A priority patent/MXPA05012254A/es
Priority to CA002524492A priority patent/CA2524492A1/en
Priority to AU2004248185A priority patent/AU2004248185B2/en
Priority to AT04754992T priority patent/ATE521687T1/de
Publication of WO2004111164A1 publication Critical patent/WO2004111164A1/en
Priority to IL171704A priority patent/IL171704A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis

Definitions

  • a method of hydrolyzing fats and oils to produce fatty acids having a low proportion of frans-isomer fatty acids is a method for hydrolyzing fats and oils under conditions resulting in a low proportion of frans-isomer fatty acids.
  • fatty acids is commonly understood to refer to the carboxylic acids naturally found in animal fats, vegetable, and marine oils. They consist of long, straight hydrocarbon chains, often having 12-22 carbon atoms, with a carboxylic acid group at one end. Most natural fatty acids have even numbers of carbon atoms. Fatty acids may or may not contain carbon-carbon double bonds. Those without double bonds are known as saturated fatty acids, while those with at least one double bond are known as unsaturated fatty acids. The most common saturated fatty acids are palmitic acid (16 carbons) and stearic acid (18 carbons). Oleic and linoleic acid (both 18 carbons) are the most common unsaturated fatty acids.
  • Trans fatty acids are unsaturated fatty acids that contain at least one double bond in the trans isomeric configuration.
  • the trans double bond configuration results in a greater bond angle than the c/s configuration. This results in a more extended fatty acid carbon chain more similar to that of saturated fatty acids rather than that of cis unsaturated double bond containing fatty acids.
  • the conformation of the double bond(s) impacts on the physical properties of the fatty acid. Those fatty acids containing a trans double bond have the potential for closer packing or aligning of acyl chains, resulting in decreased mobility; hence fluidity is reduced when compared to fatty acids containing a cis double bond.
  • Trans fatty acids are commonly produced by the partial hydrogenation of vegetable oils It has long been known that high dietary levels of saturated fatty acids are linked to increased total and low-density lipoprotein (LDL) cholesterol concentrations. More recently, however, a number of studies have reported that a diet rich in frans-isomer fatty acids not only increased LDL concentrations but also decreased high-density lipoprotein (HDL) cholesterol concentration, resulting in a less favorable overall total cholesterol/HDL cholesterol ratio (Aro et al, Am. J. Clin. Nutr., 65:1419-1426 (1997); Judd e. a/, Am. J. CHn. Nutr., 59:861-868 (1994); Judd et al, Am.
  • LDL low-density lipoprotein
  • triacylglycerols or, more commonly, triglycerides.
  • the fat or oil from a given natural source is a complex mixture of many different triacylglycerols.
  • Vegetable oils consist almost entirely of unsaturated fatty acids, while animal fats contain a much larger percentage of saturated fatty acids. Fats and oils are used in a wide variety of products, such as soaps and surfactants, lubricants, and in a variety of other food, agricultural, industrial, and other personal care products.
  • Triacylglycerols can by hydrolyzed to yield their carboxylic acids and alcohols.
  • the reaction products produced by the hydrolysis of a fat or oil molecule are one molecule of glycerol and three molecules of fatty acids.
  • This reaction proceeds via stepwise hydrolysis of the acyl groups on the glyceride, so that at any given time, the reaction mixture contains not only triglyceride, water, glycerol, and fatty acid, but also diglycerides and monoglycerides.
  • the Colgate-Emery Steam Hydrolysis Process (Brady, C, L. Metcalfek, D. Slaboszewski, and D. Frank, JAOCS, 65:917-921 (1988)).
  • This method, and modifications thereof use a countercurrent reaction of water and fat under high temperatures ranging from 24O 0 C to 315 0 C and high pressures in the range of 700 to 750 PSIG.
  • the Colgate-Emery process is the most efficient and inexpensive method for large-scale production of saturated fatty acids from fats and oils.
  • a tower is used to mix the fat and water to increase the efficiency of the hydrolysis reaction.
  • the fat is introduced from the bottom of a tower with a high pressure feed pump. Water is introduced from near the top of the tower at a ratio of 40-50% of the weight of the fat. As the fat rises though the descending water, a continuous oil-water interface is created. It is at this interface that the hydrolysis reaction occurs. Direct injection of high pressure steam raises the temperature to approximately 26O 0 C and the pressure is maintained at 700-715 PSIG. The increased pressure causes the boiling point of the water to increase, allowing for the use of higher temperatures, which results in the increase of the solubility of the water in the fat. The increased solubility of water provides for a more efficient hydrolysis reaction.
  • the Colgate-Emery method has not been shown to be effective in splitting heat sensitive triglycerides containing conjugated double bonds, hydroxy-containing fats and oils like castor oil, fish oils containing polyunsaturated acids and soybean oils high in unsaturated fats due the formation of by-products such as frans-isomer fatty acids and the degradation of the unsaturated fatty acids at high temperatures (Sonntag, JAOCS 56: 729A-732A (1979)). Therefore, the production of fatty acids from vegetable oils (e.g., soya, corn and peanut), which are generally high in unsaturated fats, is not recommended by this method.
  • vegetable oils e.g., soya, corn and peanut
  • the present invention addresses these needs by providing a method of hydrolyzing fats and oils high in unsaturated fat whereby the fatty acid products have a low frans-isomer fatty acid content suitable for use in the food industry.
  • Methods are provided for production of fatty acids by the hydrolysis of a glycerol fatty acid ester-containing composition, such as a fat and/or an oil, under reaction conditions that result in the production of fatty acid products having a low proportion of trans- ' isomer fatty acids.
  • the low frans-isomer fatty acid product typically is further processed to first separate the oil phase from the aqueous phase and removing fatty acids from the oil phase, for example, by distillation.
  • the low frans-isomer fatty acid product can then be used as a substrate for the production of 1 ,3-diacylglycerides.
  • the removal of the fatty acids from the oil phase leaves a glycerol fatty acid ester-containing residue phase that can be recycled for use as a starting material for subsequent hydrolysis reactions, typically be mixing the residue phase with additional glycerol fatty acid ester-containing composition.
  • low trans- ⁇ somer fatty acids produced by the hydrolysis of fats and/or oils high in unsaturated fats.
  • the low frans-isomer fatty acids are used in the production of food products such as cooking oils.
  • Figure 1 is a graph showing the increase in formation of frans-isomer fatty acids at various temperatures and various times.
  • 280 g RBD (refined/bleached/deodorized) of soy oil (0.8% frans-isomer content) was reacted with 420 g of water at 220 0 C (black stars), 225 0 C (gray stars), 23O 0 C (white triangles), 235 0 C (gray squares), and 25O 0 C (black diamonds) for 0-6 hours.
  • the frans-isomer formation was determined by gas chromatography. This data shows that frans-isomer formation is dependent on reaction temperature and time.
  • Figure 2 is a graph showing the split ratio (% fatty acid formed) at various temperatures and various times.
  • 280 g of RBD (refined/bleached/deodorized) soy oil (0.8% fra ⁇ s-isomer content) was reacted with 420 g of water at 225 0 C (gray stars), 23O 0 C (white triangles), 235 0 C (gray squares), and 25O 0 C (black diamonds) for 0-6 hours.
  • the degree of hydrolysis was determined by titration of fatty acids with potassium hydroxide (KOH). This data shows that an efficient hydrolysis reaction can be achieved at temperatures below 300 0 C in a reasonable reaction time.
  • a novel method is provided for the production of fatty acids having low trans- isomer fatty acid content through the hydrolysis of glycerol fatty acid ester-containing compositions, such as fats and/or oils.
  • hydrolysis refers to the separation of a glycerol fatty acid ester-containing composition, such as a fat or oil starting material, into its fatty acid and glycerin components by reacting the starting material with water. In a preferred embodiment, this reaction is non-catalytic.
  • the hydrolysis reaction may be conducted in a batch, continuous or semi- continuous method depending on the needs of the user.
  • Batch hydrolysis methods refer to the method of taking all the reactants at the beginning of the hydrolysis reaction and processing them according to a predetermined course of reaction during which no material is fed into or removed from the batch reactor (Perry's Chemical Engineers' Handbook, p. 4-25, Sixth Edition (1984)).
  • Continuous hydrolysis methods refer to methods in which reactants are introduced to the reaction and products are simultaneously withdrawn from the reaction in a continuous manner. This method is commonly used in large-scale production facilities (Perry's Chemical Engineers' Handbook, p. 4-25, Sixth Edition (1984)).
  • Semi-continuous hydrolysis methods refer to methods that are neither batch nor continuous in nature. In one embodiment, some of the reactants are changed at the beginning, and the remaining reactants are introduced and the reaction progresses. In other embodiments, the reactions products are removed continuously from the reactor (Perry's Chemical Engineers' Handbook, p. 4-25, Sixth Edition (1984)).
  • the hydrolysis reaction may incorporate an agitation or countercurrent flow method to increase the efficiency of the reaction. This can be done either by mechanical means or by the countercurrent method described in the Colgate-Emery method.
  • the amount of water used in the hydrolysis reaction is based upon the weight of the starting material.
  • One embodiment of the invention uses a minimum of three moles of water for every one mole of starting material. In a preferred embodiment, the ratio of water to starting material is 1.5 g water to 1 g starting material.
  • the hydrolysis reaction can be performed over a temperature range of about
  • a preferred temperature range for hydrolysis is from about 22O 0 C to about 25O 0 C.
  • a more preferred temperature range for hydrolysis is from about 225 0 C to about 235 0 C.
  • An even more preferred temperature for hydrolysis is about 23O 0 C.
  • the hydrolysis reaction can be performed in a batch method over a time range of about 0 hours to about 6 hours.
  • a preferred time range for batch hydrolysis is from about 2 hours to about 4 hours.
  • a more preferred time for batch hydrolysis is about 3 hours.
  • the semi-continuous and continuous methods allow for perpetual processing due to the continuous introduction of starting materials and water to the reaction.
  • split yield and “split ratio” are used interchangeably and refer to the percentage of free fatty acids produced by the hydrolysis reaction. As used herein, the terms refer to the fatty acid content of the oil phase.
  • the phrases "high split yield” or "efficient hydrolysis” are interchangeable and defined as split yields greater that 80%. More preferably, the split yield produced by the process of the invention is greater than 90%, more preferably greater than 91 %, more preferably greater than 92%, more preferably greater than 93%, more preferably greater than 94%, more preferably greater than 95%, more preferably greater than 96%, more preferably greater than 97%, more preferably greater than 98%, more preferably greater than 99%.
  • Fatty acids with a low frans-isomer fatty acid content can also be obtained with low split yields.
  • fatty acids with a low frans-isomer fatty acid content are produced by a hydrolysis reaction with a split yield less than 80%, with a split yield less than 70%, with a split yield less than 60%, with a split yield less than 40%, or with a split yield less than 20%.
  • starting materials include one or more refined or unrefined, bleached or unbleached and/or deodorized or non-deodorized fats or oils.
  • the fats or oils can comprise a single fat or oil or combinations of more than one fat or oil.
  • the fats or oils either can be saturated, mono-unsaturated or poly-unsaturated or any combination thereof.
  • saturated refers to the presence of carbon-carbon double bonds within the hydrocarbon chain.
  • the starting material is mono-unsaturated or poly-unsaturated vegetable oil.
  • the starting material is a poly-unsaturated vegetable oil.
  • the one or more unrefined and/or unbleached fats or oils can comprise butterfat, cocoa butter, cocoa butter substitutes, illipe fat, kokum butter, milk fat, mowrah fat, phulwara butter, sal fat, shea fat, borneo tallow, lard, lanolin, beef tallow, mutton tallow, tallow or other animal fat, canola oil, castor oil, coconut oil, coriander oil, corn oil, cottonseed oil, hazlenut oil, hempseed oil, linseed oil, mango kernel oil, meadowfoam oil, neat's foot oil, olive oil, palm oil, palm kernel oil, palm olein, palm stearin, palm kernel olein, palm kernel stearin, peanut oil, rapeseed oil, rice bran oil, safflower oil, sasanqua oil, soybean oil, sunflower seed oil, tall oil, tsubaki oil, vegetable oils, marine oils
  • the phrase "high in unsaturated fats” includes fats and oils, or mixtures thereof, with an iodine value of greater than 110 as determined by the Wijs method.
  • the term "iodine value” is defined as a measure of the total number of unsaturated double bonds present in a fat or oil.
  • the fat or oil subjected to hydrolysis according to the present invention has an iodine value of above 120, more preferably above 130, more preferably above 135, and more preferably above 140.
  • fatty acid as used herein is applied broadly to carboxylic acids which are found in animal fats, vegetable and marine oils. They can be found naturally in saturated, mono-unsaturated or poly-unsaturated forms.
  • the natural geometric configuration of fatty acids is c/s-isomer configuration. The c/s-isomer configuration contributes significantly to the liquidity of these acids.
  • frans-isomer fatty acids is defined as unsaturated fatty acids that contain at least one double bond in the trans isomeric configuration.
  • the phrases "low proportion of frans-isomer fatty acid” or “low frans-isomer fatty acid content” mean that the proportion of frans-isomer fatty acids found in the fatty acid product of the hydrolysis reaction of the present invention is less than 6% of the total fatty acid composition of the fatty acid product.
  • the frans- isomer fatty acid content of the fatty acids produced by the hydrolysis of the invention is less than 5% of the total fatty acid product, more preferably less than 4%, more preferably less than 3%, more preferably less than 2%, more preferably less than 1.5%.
  • the term fatty acid product refers to the product of the hydrolysis reaction that comprises the free fatty acid component of the starting material.
  • the process of the invention will yield a fatty acid product with less than a 3% increase in frans-isomer fatty acid content as compared to the frarjs-isomer fatty acid content of the starting material, more preferably less than 2.5% increase, more preferably less than 2% increase, more preferably less than 1.5% increase, more preferably less than 1% increase.
  • the process of the invention further includes separating the free fatty acids (contained in the oil phase) from the reaction mixture (aqueous phase).
  • oil phase refers to the non-aqueous phase of the product of the hydrolysis reaction. Initially, the oil phase must be separated from the aqueous phase. Common methods of separation include centrifugation, distillation or settling. Upon separating the oil and aqueous phases, the free fatty acids are further separated from the other components of the oil phase. This is accomplished by distilling the oil phase, which results in the production of a distillate (containing free fatty acids) phase and a residue phase.
  • the residue phase of the distillation process comprised mainly of mono-acylglycerides, di-acylglycerides and tri-acylglycerides, may be further processed to extract additional fatty acids.
  • This further processing includes recycling the residue product back through the hydrolysis process.
  • the fatty acid products of this invention can be further processed to produce low saturated, low transAsomer fatty acid.
  • This further processing includes coupling the hydrolysis method described herein with a method for removing saturated fatty acids via low temperature crystallization. More particularly, the process includes the mixing of the fatty acid product with a polyglycerol ester crystal modifier and subjecting the mixture to winterization in order to separate saturated fatty acids from unsaturated fatty acids.
  • the term "winterization” refers to the process of cooling oil to low temperatures until the high melting point molecules form solid particles large enough to be filtered out. Winterization is a specialized form of the overall process of fractional crystallization.
  • the fatty acids produced by the methods of the present invention are used to make 1,3-diacylglycerol.
  • the fatty acids products of the hydrolysis reaction of the present invention are treated with an enzyme, such as a lipase, which catalyzes esterification or transesterification of the terminal esters in the 1 and 3 positions of a glyceride.
  • the products of esterification or transesterification may be further used in the production of food products.
  • the fatty acids produced by the methods of the present invention are further processed by hydrogenation.
  • hydrogenation refers to the addition of hydrogen to double bonds of unsaturated fatty acids. This reaction is carried out by reacting the fatty acid product with gaseous hydrogen at elevated temperature and pressure.
  • the present invention is directed to a fatty acid composition having a low proportion of frans-isomer fatty acids prepared by the methods of the invention.
  • the present invention is directed to a cooking oil containing the low frans-isomer fatty acid compositions of the present invention.
  • the present invention is directed to foods containing the low frans-isomer fatty acid compositions of the present invention.
  • Example 1 shows that starting material high in unsaturated fats can be hydrolyzed non-catalytically to produce a fatty acid product with low trans- isomer fatty acid content.
  • the following examples are illustrative only and are not intended to limit the scope of the invention as defined by the appended claims.
  • the frans-isomer fatty acid content was 1.8% (gray stars).
  • the results from this example demonstrate that by controlling the temperature and the time of the hydrolysis reaction, a fatty acid product can be obtained with low frans-isomer fatty acid content.
  • Figure 2 summarizes the results. After 3 hours at 25O 0 C, the split yield was 95% (black diamonds). After 3 hours at 235 0 C, the split yield was 95% (gray squares). After 3 hours at 23O 0 C, the split yield was 93% (white triangles). After 3 hours at 225 0 C, the split yield was 90% (gray stars). The results demonstrate that efficient hydrolysis can occur at temperatures below 300 0 C.
  • Example 3 The following example demonstrates the ability to further process the fatty acid product of the presently claimed hydrolysis reaction by recycling the residue portion of the fatty acid product after it has been purified by evaporation.
  • 280 g of RBD (refined/bleached/deodorized) soy oil (0.8% frans-isomer content) was reacted with 420 g of water in a 1-L high pressure reactor. After a 3 hour reaction at 230 C, the split ratio and frans-isomer level were determined to be 92% and 2.1 %, respectively.
  • the upper phase of the hydrolysis reaction (fatty acid portion) was separated and purified by distillation. The distillate and residue were 87 parts and 13 parts, respectively. The distillate was 99% pure fatty acid.
  • the residue was recycled back to the fat-splitting step for 5 cycles. During the 5 recycling steps, the average split ratio was 92%. There was no significant change in fatty acid composition, including frans-isomer formation, during the 5 recycles.

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  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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PCT/US2004/018586 2003-06-10 2004-06-10 Method for the production of fatty acids having a low trans-fatty acid content WO2004111164A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
JP2006533720A JP4571144B2 (ja) 2003-06-10 2004-06-10 トランス脂肪酸含有量の低い脂肪酸を製造する方法
BRPI0410668-7A BRPI0410668B1 (pt) 2003-06-10 2004-06-10 Método para a produção de ácidos graxos tendo um baixo teor de ácido trans-graxo
KR1020057022439A KR101050437B1 (ko) 2003-06-10 2004-06-10 낮은 트랜스-지방산 함량을 가진 지방산의 제조 방법
EP04754992A EP1631649B1 (en) 2003-06-10 2004-06-10 Method for the production of fatty acids having a low trans-fatty acid content
MXPA05012254A MXPA05012254A (es) 2003-06-10 2004-06-10 Metodo para la produccion de acidos grasos que tienen un contenido bajo de acidos grasos trans.
CA002524492A CA2524492A1 (en) 2003-06-10 2004-06-10 Method for the production of fatty acids having a low trans-fatty acid content
AU2004248185A AU2004248185B2 (en) 2003-06-10 2004-06-10 Method for the production of fatty acids having a low trans-fatty acid content
AT04754992T ATE521687T1 (de) 2003-06-10 2004-06-10 Verfahren zur herstellung von fettsäuren mit geringem trans-fettsäuregehalt
IL171704A IL171704A (en) 2003-06-10 2005-10-31 Method for the production of fatty acids having a low trans-fatty acid content

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47704303P 2003-06-10 2003-06-10
US60/477,043 2003-06-10

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WO2004111164A1 true WO2004111164A1 (en) 2004-12-23

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US (1) US7126019B2 (ko)
EP (1) EP1631649B1 (ko)
JP (1) JP4571144B2 (ko)
KR (1) KR101050437B1 (ko)
CN (1) CN1802428A (ko)
AR (1) AR046492A1 (ko)
AT (1) ATE521687T1 (ko)
AU (1) AU2004248185B2 (ko)
BR (1) BRPI0410668B1 (ko)
CA (1) CA2524492A1 (ko)
IL (1) IL171704A (ko)
MX (1) MXPA05012254A (ko)
PL (1) PL379494A1 (ko)
RU (1) RU2005141141A (ko)
TW (1) TW200503634A (ko)
WO (1) WO2004111164A1 (ko)

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US8323934B2 (en) 2005-10-06 2012-12-04 Kao Corporation Process for producing fatty acids
US8491856B2 (en) 2007-07-30 2013-07-23 H R D Corporation System and process for production of fatty acids and wax alternatives from triglycerides

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US20110076358A1 (en) * 2008-05-29 2011-03-31 Kao Corporation Process for producing diacylglycerol-rich fat or oil
US8227010B2 (en) * 2008-10-10 2012-07-24 Kao Corporation Process for producing oil and fat rich in diacylglycerol
PT2636307E (pt) * 2012-03-07 2015-02-17 Cargill Inc Método de produção de composição antimicrobiana contendo ácidos gordos livres
KR102327852B1 (ko) * 2013-07-22 2021-11-18 에스케이에코프라임 주식회사 지방을 이용한 지방산알킬에스테르의 제조방법
CN103937616B (zh) * 2014-05-06 2015-06-10 江西西林科股份有限公司 一种从大豆油中提取高纯不饱和脂肪酸的方法
CN112980591B (zh) * 2019-12-12 2024-07-05 丰益油脂科技有限公司 低碘值脂肪酸产品的制备方法和低碘值脂肪酸产品
CN111004821A (zh) * 2019-12-31 2020-04-14 安徽省瑞芬得油脂深加工有限公司 一种环境友好的脂肪酸制备方法
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CN101278054B (zh) * 2005-10-06 2011-12-14 花王株式会社 制造脂肪酸的方法
US8323934B2 (en) 2005-10-06 2012-12-04 Kao Corporation Process for producing fatty acids
US8491856B2 (en) 2007-07-30 2013-07-23 H R D Corporation System and process for production of fatty acids and wax alternatives from triglycerides

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EP1631649A1 (en) 2006-03-08
KR101050437B1 (ko) 2011-07-19
BRPI0410668A (pt) 2006-06-20
IL171704A (en) 2010-12-30
AU2004248185B2 (en) 2010-03-25
AU2004248185A1 (en) 2004-12-23
JP2007503524A (ja) 2007-02-22
MXPA05012254A (es) 2006-02-10
PL379494A1 (pl) 2006-10-02
US7126019B2 (en) 2006-10-24
EP1631649B1 (en) 2011-08-24
CA2524492A1 (en) 2004-12-23
AR046492A1 (es) 2005-12-14
US20040267035A1 (en) 2004-12-30
JP4571144B2 (ja) 2010-10-27
TW200503634A (en) 2005-02-01
KR20060037257A (ko) 2006-05-03
ATE521687T1 (de) 2011-09-15
BRPI0410668B1 (pt) 2014-10-29
RU2005141141A (ru) 2006-05-27
CN1802428A (zh) 2006-07-12

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